An efficient stereoselective synthesis of methyl (S)-3-amino-3-(3-pyridyl)propanoate

Tetrahedron Letters

Volumn 40, Issue 44, 1999, Pages 7721-7725

  Zhong, H Marlon ^a   Cohen, Judith H ^a   Abdel Magid, Ahmed F ^a   Kenney, Birdella D ^a   Maryanoff, Cynthia A ^a   Shah, Rekha D ^a   Villani Jr , Frank J ^a   Zhang, Fan ^a   Zhang, Xini ^a  

^a R W JOHNSON PHARMACEUTICAL RES I   (United States)

Author keywords

Amino acid derivatives; Enamines; Stereoselective reductions

Indexed keywords

3 [1 [3 (4 PIPERIDINYL)PROPIONYL]NIPECOTOYLAMINO] 3 (3 PYRIDYL)PROPIONIC ACID; 3 AMINO 3 (3 PYRIDYL)PROPANOIC ACID METHYL ESTER; AMINO ACID DERIVATIVE; ENAMINE; FORMIC ACID DERIVATIVE; PALLADIUM; SILANE DERIVATIVE; UNCLASSIFIED DRUG;

ARTICLE; CATALYST; CHEMICAL MODIFICATION; HYDROGENATION; PARTIAL DRUG SYNTHESIS; REDUCTION; STEREOCHEMISTRY;

EID: 0033615796     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4039(99)01634-2     Document Type: Article

References (19)

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18. 12. All new compounds prepared were characterized by spectroscopic methods and elemental analysis. The enantiomeric excess (ee) was determined by chiral HPLC analysis.
19. 2. After 2 h, HPLC analysis showed the completion of the reaction. The volatiles were removed on a rotavapor at 50°C. The residual oil was diluted with EtOAc (20 mL) and MeOH (5 mL) and treated with 5.5 M HCl in MeOH (5.8 mL, 31.8 mmol). The excess MeOH was removed by evaporation on a steam-bath until the solution became cloudy again. The mixture was then stirred at rt overnight (ca. 16 h). More EtOAc (30 mL) was added to the suspension and the mixture was stirred for an additional 2 h. The solid was collected by filtration, washed with EtOAc (30 mL), and dried in vacuo for 1 h. The product 2 was obtained as a white powder (2.52 g, 94% yield, mp: 197.5-199.0°C).